Back to Hell
by dragonforest
Summary: Dean dies and gets sent back to hell. There he comes across familiar faces that might just drive him mad, and on top of that more people have taken an intrest in him. Can his friends and family save him or will he end up giving them the answer they want. Takes place around season 5, so Sam hasn’t been to hell.
1. Again

***I have never written a fanfic before so I'm sorry if it's not that good please bare with me thanks**

 **THIS IS NOT FINISHED PLEASE KEEP READING** *

 **Dean POV**

So here I am, alone and dying. My brother isn't here neither is Bobby not even Castiel. I don't even remember what happened all that clearly. All I remember was fighting the demon and the next thing I knew I was on the ground bleeding and there was a lot of blood. I'm just so cold and tired. Too tired to move, too tired to even look up to see who was calling my name.

"DEAN!" the voice screamed "DEAN." I managed to turn my head a little to see who was calling my name it was Sam.

"Sammy" I rasped.

"Bobby I found Dean he's over here" Sam shouted as he ran towards me and Bobby quickly followed so did Castiel. Suddenly Castiel appeared right beside me, his smile slowly fading.

"What's wro..." Sam started but then he saw what Castiel was looking at, Bobby soon joined them and lost his smile as well.

"Dean what happened" Castiel asked, his stare burring into me; the demon then returned.

"Oh look who finally showed up and just in time to see your precious Dean die" the demon laughed.

"So your the one who did this to Dean" Castiel hissed. Picking up the demon knife from where I had dropped it he started to walk towards the demon.

"Cas no" I managed to yelp. Castiel was just about to stab the demon, but he stopped and turned to face me.

"What do you mean no" Castiel said.

"I-I don't want the last thing I see... to be someone killing something" I said with a shaky voice.

"It won't be the last thing you see Dean. I'll heal you once I kill him" Castiel promised turning back around to face the demon, but I knew better, my wound was too deep, I knew I only had a couple of minutes left. Castiel then stabbed him. The demon's meat suit fell to the ground and Castiel had vanished and appeared next to me a couple of seconds after.

" I...I'm sorry" I whispered. Everything went black as I heard someone distantly screaming my name.

I awoke to the sound of people screaming and begging for mercy. I turned my head to see where it was coming from and where I was, that's when I realized where I was, I Dean Winchester was back in hell and back on the rack.

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ ***and that's the end of the first chapter I know it's short but I hope you enjoyed it and please keep reading***


	2. How did i let this happen

**Castiel POV**

How could I have let this happen? How could I have let him slip through my fingers? I had promised him that I would save him, why couldn't I have just left the demon alone Dean was dying and I chose to kill the demon rather than save him and now Dean's dead and it's all my fault.

"Cas" Sam shouted "CAS." I looked up at him.

"Can't you just bring him back?" Sam asked

"No, not without going to where ever he is and dragging him back"

"But you did it before, you went to hell and dragged him out" Sam yelled

"Yes but that took more than 200 angels just to get me through" I snapped

"then I'll help you and who says he's in hell" Sam cried.

"Sam if Dean was in heaven I would feel a new soul entering" I sighed with tears staring to form but I pushed them back. "I'll go get Dean, it'll be too dangerous for you there"

"Hello... I'm here to" Bobby interrupted but no one seemed to notice.

"No I'm coming and you can't stop me" Sam objected "please he's my brother."

"Fine but if I think it's too dangerous I will send you back are we clear"

"Crystal" Sam agreed.

"I assume you're coming too" I turned and asked Bobby.

"who do ya think I am, corse I'm coming, I ain't gonna stay behind ya igits " Bobby stated.

When we got back to the motel Sam and Bobby started packing everything we would need to fight the demons. I first placed Dean on the bed, I stared at him for a moment then started to stroke his cheek, it was cold. I then grabbed his bag and started to go through the contents, there was salt rounds add just regular rock salt, a rifle, a slightly faded pistol, a pure silver knife, silver bullets, a couple lighters, a couple bottles of holy water and lastly the old demon knife Sam had gotten from the demon Ruby. I knew when we got Dean back he would want the knife so I pocketed the knife and dropped the bag in front of the others.

"Will we need any of this" I asked

"Yeah just the demon knife, some holy water and salt" Sam stated without paying much attention. So I grabbed salt and a few bottles of holy water and placed them in the bag we were taking. Sam then zipped up and threw the bag over his shoulder.

"Ok let's go" Bobby nodded in my direction. I grabbed their shoulders and we were in hell.

"Let's go get Dean" I whispered taking a deep breath.

 ***I know the chapters are short but I hope to make the next chapter longer***


	3. Chapter 3

Dean POV

"So what thing should we do first, we could start by peeling your skin off one small piece at a time, we could rip out your teeth one by one or we could break every one of your bones one at a time. I'll even let you pick" the demon sneered as he walked in. I glared at him.

"Ok peeling your skin it is then" he chuckled. He then picked up a knife and made a deep cut in my wrist, then started ripping the skin from my body and it hurt lol a son of a bitch. I tried to hold in the scream that was forming in the back of my throat but it forced its way out. I let out a loud ear piercing scream that wouldn't stop.

After he had peeled half of my skin off, he picked up another knife and started to make deep incisions along my stomach and chest. I then passed out because the pain was just too much.

I awoke the next day intact and remembered where I was, that's when the demon walked in for another day of torturing me.

"Dean I'm so glad your up and ready to get to work" the demon exclaimed as he got to the table with the things that he used to torture me with. The first thing he did was grab a gun filled with rock salt and started firing it at me, I winced.

"that all you got" I taunted while coughing a little.

"Oh Dean Dean Dean, I'm just getting warmed up"

the demon declared as he picked up a knife and slashed my leg almost hitting the bone. He then grabbed a new tool, a metal bar and stuck it into what looked like an oven. After awhile he pulled it out it; was glowing. I started to tugged at the restrains but nothing happened. He then advanced on me with a devilish grin and thrusted the glowing bar into my torso.

I could hear my skin sizzling as well as smell my flesh burning. For a moment it felt warm but it soon started to hurt like hell I let out another scream. He kept on heating the metal over and over pressing it into my body, and with every scream he laughed.

"Oh I do love it when they scream" the demon muttered just loud enough for me to hear as he pushed the burning metal deeper into my chest, I winced but held in another scream.

"It's ok Dean you don't have to hold back" a different voice said walking towards me, I looked up and glared at the person in front of me. I took me a couple of seconds to process who the person was and then it clicked.

"Crowley" I clenched my jaw, of course he was here I knew he'd come torture me himself at some point. He grabbed a knife and started towards me grinned and with three small strides he was in front of me.

"I've waited a long time for this Dean and now here you are" he chuckled then dug the knife deep into my shoulder. I gritted my teeth as he then carved a symbol into my shoulder, he stepped back and was just about to say something when I blacked out.


	4. Chapter 4

**I'm so sorry this took so long to update! I've been having so trouble with my account and school took so much of my time I didn't really have time to write this chapter. It's not as long as I would have liked but it's better than nothing and I will try to update as soon as I can.**

 **Thank you all for reading this it means a lot to me and I never thought anyone would want to read this so thank you guy so much!!**

 **And without further ado here is the chapter**

 **~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~**

 **Sam POV**

When we arrived in hell, it took my eyes a second to adjust because of the sudden change in the amount of light, there had been much more light at the motel. The air was warm and thick, smelling sulfury with a hint of a blood smell. The ground was a red dirt like substance mixed with rocks and there was a building in the distance.

After briefly looking at my surroundings I turned on my heel glancing at Bobby who was on high alert looking to make sure no demon would jump us, before staring at Cas who seemed to be checking out the surroundings as well.

"Ok so which way to Dean?" I asked as a defining scream filled my ears, I had only heard that scream a couple of times in my life. It was Dean. I immediately stared at Cas trying to make eye contact but it was useless. He just stared in the direction of where the scream had come from. He looked horrified, furious and no doubt ready to smite the person responsible.

Another ear-splitting scream came and Bobby grabbed Cas before he could do anything stupid. "Cas no. We gotta come up with a plan first, and you rushing in there won't help him."

"Bobby. Dean is suffering in there and he needs me. I can't just stand here and do nothing except listen to his screams!"

Grabbing Cas by the shoulders I looked him in the eye "Cas, I know this is hard and believe me it's killing me too, but we gotta do what's best for Dean and right now that's coming up with a plan."

In the momentary silence, another blood curdling scream rang out.

I saw Bobby close his eyes and take a deep breath. This must be really hard for him too because he's basically been Dean and my dad ever since we were little. Every time Dad would leave on another hunting trip Bobby would call and make sure we were ok and if we needed anything. Dean being Dean and not wanting to accept someone's help, told him we were fine and would be until our dad came back, but that didn't stop Bobby from checking in every once and awhile.

Opening his eyes, Bobby looked at me with determination in his eyes "Alright boy, what's yer plan?"

"Ok so—" I whipped my head in the direction of the sound of something hitting the ground. It was Cas, he was sitting on his knees with his hands gripping his ears, head down and rocking back and forth. "Cas! What's wrong? What happened?"

"I-I c-can't Sam. D-Dean he's—" he let out a loud sob. "He's p-praying to me Sam! He's screaming for help and asking m-me not to leave him alone." Bobby knelt down next to him and rubbed his back until he had calmed down a little.

"Cas it'll be alright, we're gonna be with Dean soon. Dean can hold out for a little longer, he did survive forty years in hell before."

"Yeah, and when we bust in there you can smite all those sons o' bitches in there." Bobby added.

With that Cas climbed to his feet with a look of determination and nodded.

 **Dean POV**

I awoke with a sharp pain in my shoulder; it was bearable. I looked at my chest, legs, feet and as I suspected I was fully intact except for a couple of burn marks and obviously whatever Crowley did to my shoulder that was all that was left from yesterday.

Hearing rattling and a chuckle I looked up to see if the demon was back for his fun. It was pathetic really nothing compared to what I felt last time I was in the pit that demon back then was way more skilled at torture than this stupid demon. This demon was barley scratching the surface, getting some small scream out of me every now and then. It was so pathetic I almost pity them.

I was pulled out of my thoughts when the demon looked up and our eyes met. "Oh Dean you're back! Ready to have some real fun."


	5. Chapter 5

**Dean's POV** (this is a continuation from the last chapter)

 _No._

 _No. no no nonononono_

 _This isn't real._

 _He's dead._

 _Sam killed him._

 _Just take a deep breath._

 _In._

 _And out._

 _It's not working. Why isn't it working!_

 _Oh I'm holding my breath I should probably not do that. That would help._

 _Stupid stupid stupid._

 _In and out._

 _Ok good, I can breathe. Ok, it's just a hallucination._

I shut my eyes, I hear a chuckle then open them again.

 _He's still here._

 _No, NO! He's dead he can't be here! How the fuck is he here! Sam told me that he's dead Cas saw Sam kill him._

 _Ok I gotta calm the fuck down._

"So Dean-o it's just you and me again. Remember all the fun times we had together?" He asked with a twisted grin, coming closer so that he was standing only 6 feet away from me.

I glare and spit at him, it only just managing to hit his face.

"Well guess what?" He giggled, using his thumb to wipe the spit off. I clench my jaw not bothering to answer him. "Oh come on Dean don't be like that. It's no fun when you don't participate." He pauses waiting for a response.

When I still don't answer he takes a couple steps closer. "Fine I'll just tell you." He lets out another creepy giggle; a chill runs down my spine. "I know you were sad when our fun ended last time, but this time it doesn't have to end, and there's still so much more I have to teach you."

I raise my head and look him in the eyes. I lick my lips then give him a smirk. "Bite me bitch."

"Oh don't you worry Dean, we'll get there soon enough. But first let's have some other fun."

 _Shitshitshit Fuck. Shit. Ok, ok it'll be fine, you've been through this before you can handle it._

He walks slowly back over to the table. "You know Dean, I've had a lot of time to think, and I realize, I was too easy on you and yet you still broke in only 30 years." He straightens his tools. "So this time, I'm not gonna hold back and we'll see how long you last this time. I'm betting," He pauses again, picking up a pair of brass knuckles. "Maybe 20 years give or take." Walking over to me; he slips the brass knuckles on.

 _Brass knuckles, heh he's gonna have to do a lot better._

The first punch lands connecting with my jaw.

 _'t's not too bad, I've been punched plenty o' times._

Thats when my skin started to get warm.

 _Warmer._

 _Really warm_.

I ran my tongue across my bottom lip, tasting that familiar metallic flavor.

Another punch to my face. I spat out some blood that was in my mouth.

 _Hot._

 _Very hot._

 _Burning hot._

I grunted as I got a blow to my stomach.

The next one probably broke a rib or two.

 _Son of a bitch that hurts._

"Come now you don't have to keep silent. I just love to hear that lovely voice of yours"

Punch.

 ** _Yeah Dean go on, make noises. you're such a wimp. Can't even handle a couple of punches_**

 _Who said that? It sounded like dad, but it can't be he's not here._

Punch.

 ** _How can you even take care of Sam like this. You're so stupid. You had one job and you and you can't even do that right._**

 _No. I take care o' Sammy. Always take care o' Sammy._

The next punch landed and made me cough up a little blood.

 _How many was that now? 17? 30? I don' know. Lost count._

"Ok Dean-o I think we should move on to something a little more fun. Don't you?"

"I would say 'go ta hell' but we're already here"

"That filthy mouth of yours." He smirks. "Now we're getting somewhere." Walking back over to the table; he pulls the brass knuckles off.

 _Bobby, Sammy._

 _Cas._

He starts to hum to himself a tune I don't quite recognize, while his fingers dance around picking his next weapon.

A dagger, that's what he chose.

"You gonna carve me up, that it? Wow you've really lost your touch ay." I chuckle. "But I guess that's what we outta expect."

 _Why am I tryin'a provoke him._

 ** _Because deep down you know you deserve this. You know you're just a useless little fag._**

First he dips the dagger in holy water, pours salt on it then turns to face me.

"I'm not a demon, so the holy water and salt an't gonna do shit."

"Oh you naive boy. We're in hell! So according to the rules you're technically a demon."

Sauntering back over to me another one of his creepy grins comes across his face. Soon after, he starts his carving.

 _It burns._

I scream as the dagger glides it's way across my chest; blood seeping it's way down.

A gash on my thigh.

Another couple on my arms and calves.

 _It hurts. It hurts so fucking much, and the salt and holy water really aren't helping._

 _Cas, please if you can hear me I need your help man, I-I need you to get me outta here. Please Cas._

 ** _You worthless piece of shit. Yeah go cry to your little boyfriend you pansy. Always knew you were a sissy, can't even talk a little pain._**

He dips the dagger in holy water again and sprinkles it with more salt then makes his way back to my lower stomach and carves one last thing.

The cuts are deep and are sizzling. They look like they form some word. He laughs as he backs away admiring his work.

That's when it hits me.

 _Toy._


End file.
